Hydroquinone is a dihydric phenol having two hydroxyl groups on a benzene ring, which is an important compound as industrial chemicals such as a polymerization inhibitor, a photographic developing agent and a dye intermediate (a pigment or the like), or raw materials of a medicine, an agricultural chemical, a flavor material or the like. Meanwhile, 1,2,4-trihydroxybenzene is a trivalent phenol having three hydroxyl groups on a benzene ring, which is an important compound as an industrial chemical of an oxygen absorber or the like, or a raw material of a medicine, an agricultural chemical or the like. At present, tens of thousands of tons of these polyhydric phenols have been annually manufactured using petroleum as a raw material. However, in view of the present condition of global environment pollution, it is imperative to develop a novel production method which does not depend on petroleum.
Non-Patent Document 1 discloses a technology for producing 1,2,4-trihydroxybenzene (hereinafter referred to as THB) and hydroquinone by a chemical method using 2-deoxy-scyllo-inosose (hereinafter referred to as DOI) as a starting material. Non-Patent Document 1 discloses that THB is generated from DOI by heating under reflux in 0.5M phosphoric acid, and the obtained THB is catalytically reduced and dehydrated to obtain hydroquinone. According to the document, THB is obtained from DOI at a yield of 39%, and hydroquinone is obtained from THB at a yield of 53%.
Non-Patent Document 2 discloses a method for producing 4-hydroxycyclohexane-1,3-dione (hereinafter referred to as DHQ) from THB. According to this method, DHQ is obtained at a yield of 70% and a purity of 90% by HPLC analysis.
Non-Patent Document 3 discloses a method for producing hydroquinone from DHQ. According to this method, hydroquinone is obtained at a yield of 80%.
Non-Patent Document 4 discloses a method for producing DHQ from THB, not by a chemical method, but an enzymatic method. In Non-Patent Document 4, the yield of DHQ is not clearly stated.